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Chemical Compound Review

O-ANISIDINE     2-methoxyaniline

Synonyms: o-Aminoanisole, CCRIS 768, SureCN14598, NSC-3122, A88182_ALDRICH, ...
 
 
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Disease relevance of ortho-Methoxyaniline

  • Earlier studies have established that the rodent bladder carcinogen o-anisidine (OA) gives negative results in all of the standard rodent genetic toxicity assays [1].
  • The products of all three genes are demonstrated to catalyse acetylation of aminofluorene and anisidine following expression in Escherichia coli [2].
 

High impact information on ortho-Methoxyaniline

  • Using recombinant human CYP (in Supersomes) and purified CYPs, the participation of CYP2E1 in o-anisidine oxidation was confirmed [3].
  • Two o-anisidine-DNA adducts, identical to those found in DNA incubated with o-anisidine and human microsomes in vitro, were detected in urinary bladder (4.1 adducts per 10(7) nucleotides), the target organ, and, to a lesser extent, in liver, kidney and spleen [3].
  • The results, the first report on the potential of the human microsomal CYP enzymes to activate o-anisidine, strongly suggest a carcinogenic potential of this rodent carcinogen for humans [3].
  • This reactive metabolite of 2-NA was identified in incubations with human hepatic cytosol, besides 2-methoxyaniline (o-anisidine) [4].
  • Hepatocyte GSH was also depleted by all arylamines tested and extensive GSH oxidation occurred with o-anisidine and aminofluorene, which was prevented by CYP1A2 inhibitors [5].
 

Chemical compound and disease context of ortho-Methoxyaniline

 

Biological context of ortho-Methoxyaniline

 

Anatomical context of ortho-Methoxyaniline

 

Associations of ortho-Methoxyaniline with other chemical compounds

 

Gene context of ortho-Methoxyaniline

  • Furthermore, by induction of rat hepatic and renal CYP1A1/2, both o-nitroanisole and o-anisidine influence their carcinogenic effects, modifying their detoxification and/or activation pathways [12].
  • The data demonstrate the participation of different rat and rabbit CYP enzymes in o-anisidine oxidation and indicate that both experimental animal species might serve as suitable models to mimic the o-anisidine oxidation in human [12].
  • Carcinogenic pollutants o-nitroanisole and o-anisidine are substrates and inducers of cytochromes P450 [12].
  • The o-anisidine-DNA adducts became detectable only when DNA modified by o-anisidine was digested using three times higher concentrations of micrococcal nuclease and spleen phosphodiesterase (MN/SPD) [11].
 

Analytical, diagnostic and therapeutic context of ortho-Methoxyaniline

  • Utilizing Western blotting and consecutive immunoquantification employing chicken polyclonal anti bodies raised against various CYPs, the effect of o-anisidine and o-nitroanisole on the expression of the CYP enzymes was investigated [12].

References

  1. Mutagenicity of o-anisidine to the bladder of lacI- transgenic B6C3F1 mice: absence of 14C or 32P bladder DNA adduction. Ashby, J., Short, J.M., Jones, N.J., Lefevre, P.A., Provost, G.S., Rogers, B.J., Martin, E.A., Parry, J.M., Burnette, K., Glickman, B.W. Carcinogenesis (1994) [Pubmed]
  2. Arylamine N-acetyltransferase in Balb/c mice: identification of a novel mouse isoenzyme by cloning and expression in vitro. Kelly, S.L., Sim, E. Biochem. J. (1994) [Pubmed]
  3. Identification of a genotoxic mechanism for the carcinogenicity of the environmental pollutant and suspected human carcinogen o-anisidine. Stiborová, M., Miksanová, M., Sulc, M., Rýdlová, H., Schmeiser, H.H., Frei, E. Int. J. Cancer (2005) [Pubmed]
  4. Identification of a genotoxic mechanism for 2-nitroanisole carcinogenicity and of its carcinogenic potential for humans. Stiborová, M., Miksanová, M., Smrcek, S., Bieler, C.A., Breuer, A., Klokow, K.A., Schmeiser, H.H., Frei, E. Carcinogenesis (2004) [Pubmed]
  5. N-oxidation of aromatic amines by intracellular oxidases. Siraki, A.G., Chan, T.S., Galati, G., Teng, S., O'Brien, P.J. Drug Metab. Rev. (2002) [Pubmed]
  6. The aromatic amine carcinogens o-toluidine and o-anisidine induce free radicals and intrachromosomal recombination in Saccharomyces cerevisiae. Brennan, R.J., Schiestl, R.H. Mutat. Res. (1999) [Pubmed]
  7. Oxidative DNA damage induced by a metabolite of carcinogenic o-anisidine: enhancement of DNA damage and alteration in its sequence specificity by superoxide dismutase. Ohkuma, Y., Kawanishi, S. Arch. Biochem. Biophys. (2001) [Pubmed]
  8. Structure-activity relationships of several anisidine and dibenzanthracene isomers in the w/w+ somatic assay of Drosophila melanogaster. Rodriguez-Arnaiz, R., Téllez, G.O. Mutat. Res. (2002) [Pubmed]
  9. Tissue distribution, excretion and metabolism of o-anisidine in rats. Sapota, A., Czerski, B., Jedrzejczak, M. International journal of occupational medicine and environmental health. (2003) [Pubmed]
  10. Organ-specific genotoxicity of the potent rodent bladder carcinogens o-anisidine and p-cresidine. Sasaki, Y.F., Nishidate, E., Su, Y.Q., Matsusaka, N., Tsuda, S., Susa, N., Furukawa, Y., Ueno, S. Mutat. Res. (1998) [Pubmed]
  11. Mechanism of peroxidase-mediated oxidation of carcinogenic o-anisidine and its binding to DNA. Stiborová, M., Miksanová, M., Havlícek, V., Schmeiser, H.H., Frei, E. Mutat. Res. (2002) [Pubmed]
  12. Carcinogenic pollutants o-nitroanisole and o-anisidine are substrates and inducers of cytochromes P450. Rýdlová, H., Miksanová, M., Ryslavá, H., Stiborová, M. Biomedical papers of the Medical Faculty of the University Palacký, Olomouc, Czechoslovakia. (2005) [Pubmed]
 
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